Skip to Content
Merck
CN
All Photos(3)

Documents

Safety Information

R0395

Sigma-Aldrich

Rapamycin from Streptomyces hygroscopicus

≥95% (HPLC), powder

Sign Into View Organizational & Contract Pricing

Synonym(s):
23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, AY 22989, Sirolimus
Empirical Formula (Hill Notation):
C51H79NO13
CAS Number:
Molecular Weight:
914.17
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥95% (HPLC)

form

powder

color

off-white

solubility

ethanol: 2 mM
DMSO: soluble

antibiotic activity spectrum

fungi
yeast

Mode of action

enzyme | inhibits
protein synthesis | interferes

storage temp.

−20°C

SMILES string

CO[C@@H]1C[C@@H](CC[C@H]1O)C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC

InChI

1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

InChI key

QFJCIRLUMZQUOT-HPLJOQBZSA-N

Gene Information

human ... FKBP1A(2280)

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Chemical structure: macrolide
Rapamycin is derived from Streptomyces hygroscopicus . It can inhibit viral replication. This natural anti-fungal antibiotic is a proven anti-aging agent. Rapamycin significantly inhibits mTORC1 regardless of age. It suppresses protein kinase C activity and enhances ion transport in A6 cells. It also suppresses the immune response in membrane and cytosolic preparations. Additionally, it has specific effects on the translation of endogenous mRNAs and inhibits the translation of 5′TOP mRNAs by blocking p70s6k activation in the signaling pathway. Rapamycin exhibits antineoplastic properties.

Application

Rapamycin from Streptomyces hygroscopicus has been used:
  •  to treat BV2 cells or BV2-LC3 cells for autophagy assay
  • as an autophagy activator in the bone marrow mesenchymal stem cells (BM-MSCs) transfected with lentivirus carrier of small interfering RNA for FOXO3 (siFOXO3) to study the effects of Forkhead Box O3 (FOXO3) on the autophagy of BM-MSCs
  • to pre-incubate villi to inhibit the mammalian target of rapamycin complex 1 (mTORC1) signaling

Biochem/physiol Actions

A macrocyclic triene antibiotic that binds to and inhibits the molecular target of rapamycin (mTOR). It forms a complex with FKBP12 that binds to and inhibits the molecular target of rapamycin (mTOR). Rapamycin is a potent immunosuppressant and has anticancer activity.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2 - Repr. 2

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the solubility of Product R0395, Rapamycin?

    Rapamycin is soluble in DMSO and in methanol (each at 25 mg/mL) and in ethanol  (2 mM). It is insoluble in water. Additional solubility information is in the product information sheet (under Documents, above).

  4. How should we store solutions of Product R0395, Rapamycin?

    Rokaw, M.D. et al. J. Biol. Chem. 271, 32468 (1996) described storage of a 2 mM solution of rapamycin in ethanol at -70 °C which was diluted into serum-free media before use. Unless otherwise noted for other solvents, it may be best to prepare solutions fresh and protected from light. Please refer to our product information sheet at our website.

  5. What is the shelf life of Product R0395, Rapamycin, as received?

    The product has a recommended retest date of 2 years but the actual recommended retest date for each lot is on the Certificate of Analysis.  We guarantee the quality of the product through this date for unopened bottles stored at -20 °C.

  6. What are the extinction coefficient values for Product R0395, Rapamycin, solutions?

    The E1% extinction coefficient values in 95% ethanol at 267 nm, 277 nm and 288 nm have been reported and are listed in the product information sheet (under Documents, above).

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Rapamycin inhibits protein kinase C activity and stimulates Na+ transport in A6 cells
Rokaw MD, et al.
The Journal of Biological Chemistry, 271, 32468-32473 (1996)
FOXO3 is targeted by miR-223-3p and promotes osteogenic differentiation of bone marrow mesenchymal stem cells by enhancing autophagy
Long C, et al.
Human Cell : Official Journal of Human Cell Research Society (2021)
Activation of autophagy pathway suppresses the expression of iNOS, IL6 and cell death of LPS-stimulated microglia cells
Han HE, et al.
Biomolecules & Therapeutics, 21, 21-21 (2013)
Rapamycin for longevity: opinion article
Blagosklonny, Mikhail V
Aging (Albany. NY.), 11, 8048-8048 (2019)
Heng Liu et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 23(10), 3383-3392 (2009-06-11)
Regulator of calcineurin 1 (RCAN1), a gene identified from the critical region of Down syndrome, has been implied in pathogenesis of Alzheimer's disease (AD). RCAN1 expression was shown to be increased in AD brains; however, the mechanism of RCAN1 gene

Articles

Cancer stem cell media, spheroid plates and cancer stem cell markers to culture and characterize CSC populations.

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Related Content

Explore protein pathway analysis including chemical library screening and modulating pathways with small molecules.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service